Irresistible Milk Chocolate Stuffed Jack-O’-Lantern Cookies

Name: Milk Chocolate Stuffed Jack-O'-Lantern Cookies
Prep time: 15 min
Cook time: 12 min
Total time: 27 min
Cuisine: American
Ingredients: 2 ¼ cups all-purpose flour; 1 tsp baking soda; ½ tsp salt; ¾ cup unsalted butter (room temperature); ½ cup granulated sugar; ½ cup brown sugar (packed); 2 large eggs; 1 tsp vanilla extract; 1 cup milk chocolate chips; Orange icing (for decoration)

Published: September 15, 2025

by Molly white

Why You'll Love This Recipe

These Milk Chocolate Stuffed Jack-O’-Lantern Cookies are incredibly easy to make, so even novice bakers can impress their friends
The rich chocolate filling adds a decadent surprise in every bite
They look adorable on any dessert table and are sure to be a hit at Halloween parties
These cookies are versatile enough to customize with other fillings or decorations based on personal preferences

One time, my nephew took one bite and exclaimed that it was “the best cookie ever!” I couldn’t help but puff out my chest with pride.

Essential Ingredients

Here’s what you’ll need to make this delicious dish:

All-Purpose Flour: This is the base for our cookies; choose unbleached for better flavor and texture.
Baking Soda: A must-have for that perfect rise; don’t skip it unless you enjoy flat cookies.
Salt: Just a pinch elevates the flavors—don’t underestimate its power!
Unsalted Butter: Use room temperature butter for easy creaming and a rich taste.
Granulated Sugar: Sweetens up the dough nicely; feel free to adjust based on your preference.
Brown Sugar: Adds moisture and a hint of caramel flavor—always use both types of sugar for balance.
Large Eggs: Essential for binding everything together; fresh eggs make a world of difference.
Vanilla Extract: Use pure vanilla extract instead of imitation for richer flavor.
Milk Chocolate Chips: The star ingredient! You can substitute dark chocolate if you’re feeling adventurous.
Orange Icing (for decoration): Use store-bought for quick decorating or whip up your own if you’re feeling fancy.

The full ingredients list, including measurements, is provided in the recipe card directly below.

Milk Chocolate Stuffed Jack-O'-Lantern Cookies

Let’s Make it Together

Prepare Your Oven and Baking Sheet: Preheat your oven to 350°F (175°C) and line your baking sheet with parchment paper for easy cleanup.

Mix Dry Ingredients Together: In a bowl, whisk together flour, baking soda, and salt until well combined; this ensures even distribution.

Cream Butter and Sugars Together: In another bowl, beat softened butter with granulated and brown sugars until light and fluffy—about 3-4 minutes should do the trick.

Add Eggs and Vanilla Extract: Mix in eggs one at a time followed by vanilla extract; this creates a smooth foundation for your cookie dough.

Combine Wet and Dry Ingredients: Gradually add dry mixture into wet ingredients while mixing until just combined; be careful not to overmix or your cookies might turn tough.

Add Chocolate Chips and Chill Dough (Optional): Fold in milk chocolate chips gently. For chewier cookies, chill the dough in the fridge for about 30 minutes before baking. For more inspiration, check out this Irresistible Double Chocolate Cookies recipe.

Scoop and Shape Your Cookies: Using a tablespoon or cookie scoop, portion out dough onto prepared baking sheets. Flatten each ball slightly to create a Jack-O’-Lantern shape.

Bake Until Golden Brown: Place cookies in preheated oven for 10-12 minutes or until edges are golden brown; they will continue cooking on the baking sheet after removing from oven.

Decorate Your Cookies (Optional): Once cooled completely, use orange icing to create fun Jack-O’-Lantern faces; let creativity run wild!

And there you have it! Delicious Milk Chocolate Stuffed Jack-O’-Lantern Cookies that not only taste incredible but also bring joy to any Halloween celebration. Enjoy every gooey bite!

You Must Know

These Milk Chocolate Stuffed Jack-O’-Lantern Cookies are not just adorable; they’ll vanish faster than a ghost at midnight
The sweet aroma will have everyone flocking to the kitchen, and they’re perfect for any festive occasion while being ridiculously fun to make!

Perfecting the Cooking Process

Start by chilling your cookie dough before baking. This helps maintain shape and texture, ensuring those chocolate centers melt perfectly without becoming too flat.

Add Your Touch

Feel free to swap out the milk chocolate for dark chocolate or even peanut butter-filled chocolate for a nutty twist. You can also add orange zest for a hint of citrus.

Storing & Reheating

Store cookies in an airtight container at room temperature for up to one week. To reheat, pop them in the microwave for 10 seconds for that fresh-baked feel.

Chef's Helpful Tips

Make sure your butter is softened but not melted; it makes mixing easier
Avoid overbaking for soft, chewy centers; keep an eye on them in the oven
Chilling the dough is crucial for preventing spreading during baking

I still remember the first time I made these cookies with my niece. We ended up with more flour on our faces than in the bowl, but we laughed until our sides hurt!